WO2007045741A3 - Novel method for preparing unsaturated fatty hydroxyacids - Google Patents

Novel method for preparing unsaturated fatty hydroxyacids Download PDF

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Publication number
WO2007045741A3
WO2007045741A3 PCT/FR2006/002268 FR2006002268W WO2007045741A3 WO 2007045741 A3 WO2007045741 A3 WO 2007045741A3 FR 2006002268 W FR2006002268 W FR 2006002268W WO 2007045741 A3 WO2007045741 A3 WO 2007045741A3
Authority
WO
WIPO (PCT)
Prior art keywords
unsaturated fatty
novel method
preparing unsaturated
hydroxyacids
fatty hydroxyacids
Prior art date
Application number
PCT/FR2006/002268
Other languages
French (fr)
Other versions
WO2007045741A2 (en
Inventor
Natacha Frison
Benoit Folleas
Jean-Louis Brayer
Original Assignee
Diverchim
Natacha Frison
Benoit Folleas
Jean-Louis Brayer
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Diverchim, Natacha Frison, Benoit Folleas, Jean-Louis Brayer filed Critical Diverchim
Priority to US12/083,926 priority Critical patent/US7928254B2/en
Priority to EP06820174.8A priority patent/EP1940770B1/en
Priority to CA2626588A priority patent/CA2626588C/en
Priority to JP2008536075A priority patent/JP5220610B2/en
Publication of WO2007045741A2 publication Critical patent/WO2007045741A2/en
Publication of WO2007045741A3 publication Critical patent/WO2007045741A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention concerns a method for preparing a compound of formula (I), wherein: R3 and R1 represent in particular H and n is greater than 4, said preparation method including performing a Wittig-Horner reaction with a phosphonate on a lactol, so as to obtain a hydroxyester and, optionally a saponification reaction of said hydroxyester.
PCT/FR2006/002268 2005-10-21 2006-10-10 Novel method for preparing unsaturated fatty hydroxyacids WO2007045741A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US12/083,926 US7928254B2 (en) 2005-10-21 2006-10-10 Method for preparing unsaturated fatty hydroxyacids
EP06820174.8A EP1940770B1 (en) 2005-10-21 2006-10-10 Novel method for preparing unsaturated fatty hydroxyacids
CA2626588A CA2626588C (en) 2005-10-21 2006-10-10 Novel method for preparing unsaturated fatty hydroxyacids
JP2008536075A JP5220610B2 (en) 2005-10-21 2006-10-10 Novel process for producing unsaturated aliphatic hydroxy acids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0510765A FR2892411B1 (en) 2005-10-21 2005-10-21 NOVEL PROCESS FOR PREPARING UNSATURATED HYDROXY FATTY ACIDS
FR0510765 2005-10-21

Publications (2)

Publication Number Publication Date
WO2007045741A2 WO2007045741A2 (en) 2007-04-26
WO2007045741A3 true WO2007045741A3 (en) 2007-08-02

Family

ID=36648361

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2006/002268 WO2007045741A2 (en) 2005-10-21 2006-10-10 Novel method for preparing unsaturated fatty hydroxyacids

Country Status (6)

Country Link
US (1) US7928254B2 (en)
EP (1) EP1940770B1 (en)
JP (1) JP5220610B2 (en)
CA (1) CA2626588C (en)
FR (1) FR2892411B1 (en)
WO (1) WO2007045741A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2892410B1 (en) * 2005-10-21 2010-10-15 Fabre Pierre Dermo Cosmetique NOVEL UNSATURATED FATTY HYDRO ACIDS AND THEIR DERMO COSMETOLOGICAL USE
JP2015040202A (en) * 2013-08-23 2015-03-02 高砂香料工業株式会社 Method for producing alkene compound having acyloxy group at terminal
CN109516623B (en) * 2018-11-16 2021-06-01 浙江万盛股份有限公司 Comprehensive utilization method of tributoxyethyl phosphate wastewater
CN116041172B (en) * 2023-02-01 2024-08-02 宝鸡文理学院 Preparation method of nervonic acid

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63317091A (en) * 1987-06-18 1988-12-26 Denki Kagaku Kogyo Kk Production of omega-hydroxy-trans-alpha,beta-unsaturated fatty acid
FR2684988A1 (en) * 1991-12-12 1993-06-18 Fabre Pierre Cosmetique Industrial process for the synthesis of 10-hydroxy-2-decenoic acid and 9-oxo-2-decenoic acid, which are active principles of royal jelly

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6045623B2 (en) * 1977-12-20 1985-10-11 学校法人近畿大学 Synthesis method of royal jelly acid (10-hydroxy-trans-2-decenoic acid)
US4879420A (en) * 1988-05-06 1989-11-07 E.I. Du Pont De Nemours And Company Preparation of mixtures of butanediols
DE4134771A1 (en) * 1991-10-22 1993-04-29 Basf Ag METHOD FOR PRODUCING 2,2-BIS-HYDROXYMETHYL-BUTANDIOL- (1,4)
FR2829491B1 (en) * 2001-09-12 2005-09-30 Diverchim PROCESS FOR THE PREPARATION OF UNSATURATED FATTY HYDROXY ACIDS AND THEIR ESTERS, THEIR USE AS ANTI-COLLAGENASE AGENT

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63317091A (en) * 1987-06-18 1988-12-26 Denki Kagaku Kogyo Kk Production of omega-hydroxy-trans-alpha,beta-unsaturated fatty acid
FR2684988A1 (en) * 1991-12-12 1993-06-18 Fabre Pierre Cosmetique Industrial process for the synthesis of 10-hydroxy-2-decenoic acid and 9-oxo-2-decenoic acid, which are active principles of royal jelly

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
COLONGE ET AL: "Préparation d'homologues du décène-2 ol-10 oique", BULL. SOC.CHIM., 1963, pages 551 - 553, XP009069614 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002432342, Database accession no. BRN1867281 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002432343, Database accession no. BRN239063 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002432344, Database accession no. BRN1860078 *
J.CHEM.SOC., 1962, pages 5299 - 5301, XP009083435 *
LIST ET AL: "Practical Synthesis of (E)-alpha,beta-Unsaturated Esters from Aldehydes", ADV. SYNTH. CATAL., vol. 347, 2005, pages 1558 - 1560, XP002390820 *
RAGOUSSIS: "Stereoselektive Access to Tetrahydropyranylacetic Acid Derivatives", SYNTHESIS, vol. 1, 1993, pages 84 - 86, XP001247243 *
S.DOLEZAL ET AL, COLLECT.CZECH.CHEM.COMMUN., vol. 31, 1966, pages 3765 - 3774, XP009083434 *
VILLIERAS J ET AL: "La Reaction de Wittig-Horner en milieu heterogene VI. Selectivité de la reaction sur des composés bifonctionnels", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 26, no. 1, 1985, pages 53 - 56, XP002198720, ISSN: 0040-4039 *
YOKOI ET AL, NIPPON KAGAKU KAISHI, 1978, pages 1415 - 1417, XP009083436 *

Also Published As

Publication number Publication date
FR2892411B1 (en) 2009-03-20
WO2007045741A2 (en) 2007-04-26
EP1940770A2 (en) 2008-07-09
JP2009512665A (en) 2009-03-26
US20080281114A1 (en) 2008-11-13
JP5220610B2 (en) 2013-06-26
EP1940770B1 (en) 2015-11-11
FR2892411A1 (en) 2007-04-27
CA2626588C (en) 2014-11-25
CA2626588A1 (en) 2007-04-26
US7928254B2 (en) 2011-04-19

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